Exam 3 Chem 230 Practice Exam Dr. Bebbington F24 PDF

PRINT NAME: Exam 3 Chem 230 Practice exam Dr. Bebbington 1) The reaction of ethene with HBr produces bromoethane, shown in the equation below. Axes for a free energy diagram are shown below the equation and the reaction is exergonic. Draw the curve and the locatio...

PRINT NAME: Exam 3 Chem 230 Practice exam Dr. Bebbington 1) The reaction of ethene with HBr produces bromoethane, shown in the equation below. Axes for a free energy diagram are shown below the equation and the reaction is exergonic. Draw the curve and the location of: i) the starting materials and products ii) the reactive intermediate iii) the transition states iv) Suggest a structure for the intermediate: (10 points) 2) Rank the following carbocations in order of stability (1 = most stable, 4 = least stable): (5 points) 3) i) State Markovnikov’s rule: (5 points) ii) Draw the products from the following reactions and state whether they are examples of Markovnikov or Anti-Markovnikov addition to alkenes, including stereochemistry where necessary: (12 points) 4) Fill in the missing compounds below, indicating stereochemistry when necessary: (12 points) 5) Draw the starting material that would be required to prepare the diketone shown below by ozonolysis: (4 points) 6) Addition of HBr to the alkene below occurs with a carbocation rearrangement. Fill in the intermediates and draw a mechanism with curved arrows for each step. (12 points) 7) Assign the configuration of the two alkenes below as E or Z using IUPAC/CIP. Explain your answers (8 points): 8) Name the two alkenes below according to IUPAC rules (8 points) : 9) A student wishes to prepare the dibromo compound A shown below from bromination oof cyclohexene. A second student suggests correctly that this will not be possible. i) Draw the expected major diastereomeric product from this reaction: (4 points) ii) Explain why the product you have drawn is the only one possible with reference to the reaction mechanism (6 points): 10) Draw the starting alkenes needed for the preparation of the epoxides below in the boxes (4 points each): 11) i) Look at the polymer represented by the repeat unit below. Draw the structure of the monomer from which it was prepared: ii) Look at the monomer below. Draw the expected repeat unit of the resulting polymer. (6 points)